Displacement of sugar triflates with c-nucleophiles: D-glucopyranose and d-ribofuranose chain extension and functionalization

Q. Shen, D. G. Sloss, David B Berkowitz

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Treatment of methyl 4-O-benzyl-2,3-di-O-methoxymethyl-6-0-trifluoromethanesulfonyl-a-D-glucopyranoside 1 or 3-O-benzyl 1,2-0-isopropylidene-5-O-trifluoromethenesulfonyl-a-D-ribofuranoside 2 with a variety of functionalized C-nucleophiles in THF/HMPA leads to the corresponding chain-extended sugars in very good to excellent yields.

Original languageEnglish (US)
Pages (from-to)1519-1530
Number of pages12
JournalSynthetic Communications
Volume24
Issue number11
DOIs
StatePublished - Jun 1 1994

Fingerprint

Hempa
Nucleophiles
Sugars
propylene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Displacement of sugar triflates with c-nucleophiles : D-glucopyranose and d-ribofuranose chain extension and functionalization. / Shen, Q.; Sloss, D. G.; Berkowitz, David B.

In: Synthetic Communications, Vol. 24, No. 11, 01.06.1994, p. 1519-1530.

Research output: Contribution to journalArticle

@article{243256e4cabc4fa28b89b86427210094,
title = "Displacement of sugar triflates with c-nucleophiles: D-glucopyranose and d-ribofuranose chain extension and functionalization",
abstract = "Treatment of methyl 4-O-benzyl-2,3-di-O-methoxymethyl-6-0-trifluoromethanesulfonyl-a-D-glucopyranoside 1 or 3-O-benzyl 1,2-0-isopropylidene-5-O-trifluoromethenesulfonyl-a-D-ribofuranoside 2 with a variety of functionalized C-nucleophiles in THF/HMPA leads to the corresponding chain-extended sugars in very good to excellent yields.",
author = "Q. Shen and Sloss, {D. G.} and Berkowitz, {David B}",
year = "1994",
month = "6",
day = "1",
doi = "10.1080/00397919408010152",
language = "English (US)",
volume = "24",
pages = "1519--1530",
journal = "Synthetic Communications",
issn = "0039-7911",
publisher = "Taylor and Francis Ltd.",
number = "11",

}

TY - JOUR

T1 - Displacement of sugar triflates with c-nucleophiles

T2 - D-glucopyranose and d-ribofuranose chain extension and functionalization

AU - Shen, Q.

AU - Sloss, D. G.

AU - Berkowitz, David B

PY - 1994/6/1

Y1 - 1994/6/1

N2 - Treatment of methyl 4-O-benzyl-2,3-di-O-methoxymethyl-6-0-trifluoromethanesulfonyl-a-D-glucopyranoside 1 or 3-O-benzyl 1,2-0-isopropylidene-5-O-trifluoromethenesulfonyl-a-D-ribofuranoside 2 with a variety of functionalized C-nucleophiles in THF/HMPA leads to the corresponding chain-extended sugars in very good to excellent yields.

AB - Treatment of methyl 4-O-benzyl-2,3-di-O-methoxymethyl-6-0-trifluoromethanesulfonyl-a-D-glucopyranoside 1 or 3-O-benzyl 1,2-0-isopropylidene-5-O-trifluoromethenesulfonyl-a-D-ribofuranoside 2 with a variety of functionalized C-nucleophiles in THF/HMPA leads to the corresponding chain-extended sugars in very good to excellent yields.

UR - http://www.scopus.com/inward/record.url?scp=0028223767&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028223767&partnerID=8YFLogxK

U2 - 10.1080/00397919408010152

DO - 10.1080/00397919408010152

M3 - Article

AN - SCOPUS:0028223767

VL - 24

SP - 1519

EP - 1530

JO - Synthetic Communications

JF - Synthetic Communications

SN - 0039-7911

IS - 11

ER -